# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_202008135
_database_code_depnum_ccdc_archive 'CCDC 2094034'
loop_
_audit_author_name
_audit_author_address
'Zechao Wang'
;Zhengzhou University
China
;
_audit_update_record             
;
2021-07-02 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Br N'
_chemical_formula_weight         326.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.9270(3)
_cell_length_b                   17.7263(9)
_cell_length_c                   14.8916(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.915(4)
_cell_angle_gamma                90
_cell_volume                     1541.19(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.530
_shelx_estimated_absorpt_T_min   0.585
_shelx_estimated_absorpt_T_max   0.719
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5529
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.911
_diffrn_reflns_theta_max         67.047
_diffrn_reflns_theta_full        67.047
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2741
_reflns_number_gt                2130
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+1.5843P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2741
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1332
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.38898(9) 0.34491(4) 1.08407(4) 0.0801(2) Uani 1 1 d . . . . .
N1 N 1.0912(7) 0.4682(2) 0.8873(3) 0.0734(11) Uani 1 1 d . . . . .
C1 C 0.9070(8) 0.4566(2) 0.8926(3) 0.0527(9) Uani 1 1 d . . . . .
C2 C 0.6680(6) 0.4368(2) 0.8972(3) 0.0474(8) Uani 1 1 d . . . . .
H2A H 0.5677 0.4585 0.8452 0.057 Uiso 1 1 calc R U . . .
H2B H 0.6267 0.4582 0.9521 0.057 Uiso 1 1 calc R U . . .
C3 C 0.6340(6) 0.35220(19) 0.8975(2) 0.0401(7) Uani 1 1 d . . . . .
C4 C 0.7483(6) 0.3116(2) 0.9828(3) 0.0486(8) Uani 1 1 d . . . . .
H4A H 0.6946 0.2598 0.9794 0.058 Uiso 1 1 calc R U . . .
H4B H 0.9118 0.3104 0.9825 0.058 Uiso 1 1 calc R U . . .
C5 C 0.7111(7) 0.3442(2) 1.0726(3) 0.0551(10) Uani 1 1 d . . . . .
H5A H 0.7696 0.3954 1.0781 0.066 Uiso 1 1 calc R U . . .
H5B H 0.7965 0.3148 1.1219 0.066 Uiso 1 1 calc R U . . .
C6 C 0.5206(6) 0.3153(2) 0.8253(2) 0.0407(7) Uani 1 1 d . . . . .
C7 C 0.4364(6) 0.35048(19) 0.7341(2) 0.0425(8) Uani 1 1 d . . . . .
C8 C 0.5818(7) 0.3912(3) 0.6889(3) 0.0572(10) Uani 1 1 d . . . . .
H8 H 0.7319 0.4001 0.7173 0.069 Uiso 1 1 calc R U . . .
C9 C 0.5054(9) 0.4191(3) 0.6014(3) 0.0697(12) Uani 1 1 d . . . . .
H9 H 0.6046 0.4465 0.5718 0.084 Uiso 1 1 calc R U . . .
C10 C 0.2852(9) 0.4062(3) 0.5589(3) 0.0707(13) Uani 1 1 d . . . . .
H10 H 0.2348 0.4246 0.5004 0.085 Uiso 1 1 calc R U . . .
C11 C 0.1391(8) 0.3662(3) 0.6027(3) 0.0646(12) Uani 1 1 d . . . . .
H11 H -0.0107 0.3575 0.5739 0.078 Uiso 1 1 calc R U . . .
C12 C 0.2131(7) 0.3385(2) 0.6892(3) 0.0515(9) Uani 1 1 d . . . . .
H12 H 0.1120 0.3115 0.7182 0.062 Uiso 1 1 calc R U . . .
C13 C 0.4767(6) 0.2320(2) 0.8276(2) 0.0420(8) Uani 1 1 d . . . . .
C14 C 0.6170(7) 0.1823(2) 0.7911(3) 0.0514(9) Uani 1 1 d . . . . .
H14 H 0.7422 0.2008 0.7679 0.062 Uiso 1 1 calc R U . . .
C15 C 0.5738(9) 0.1059(2) 0.7885(3) 0.0664(12) Uani 1 1 d . . . . .
H15 H 0.6700 0.0734 0.7639 0.080 Uiso 1 1 calc R U . . .
C16 C 0.3903(10) 0.0777(3) 0.8220(3) 0.0712(13) Uani 1 1 d . . . . .
H16 H 0.3608 0.0261 0.8196 0.085 Uiso 1 1 calc R U . . .
C17 C 0.2502(9) 0.1255(3) 0.8592(3) 0.0718(13) Uani 1 1 d . . . . .
H17 H 0.1254 0.1064 0.8821 0.086 Uiso 1 1 calc R U . . .
C18 C 0.2941(7) 0.2027(3) 0.8627(3) 0.0596(10) Uani 1 1 d . . . . .
H18 H 0.1996 0.2349 0.8888 0.072 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C5 1.946(4) . ?
N1 C1 1.127(5) . ?
C1 C2 1.472(6) . ?
C2 C3 1.514(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C6 1.338(5) . ?
C3 C4 1.514(5) . ?
C4 C5 1.508(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.500(5) . ?
C6 C13 1.501(5) . ?
C7 C8 1.384(5) . ?
C7 C12 1.392(5) . ?
C8 C9 1.394(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.368(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.368(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.381(5) . ?
C13 C14 1.386(5) . ?
C14 C15 1.377(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.368(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.393(7) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 176.6(5) . . ?
C1 C2 C3 111.4(3) . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C6 C3 C4 122.2(3) . . ?
C6 C3 C2 122.0(3) . . ?
C4 C3 C2 115.7(3) . . ?
C5 C4 C3 116.7(3) . . ?
C5 C4 H4A 108.1 . . ?
C3 C4 H4A 108.1 . . ?
C5 C4 H4B 108.1 . . ?
C3 C4 H4B 108.1 . . ?
H4A C4 H4B 107.3 . . ?
C4 C5 Br1 112.1(3) . . ?
C4 C5 H5A 109.2 . . ?
Br1 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
Br1 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C3 C6 C7 124.6(3) . . ?
C3 C6 C13 121.8(3) . . ?
C7 C6 C13 113.5(3) . . ?
C8 C7 C12 117.8(3) . . ?
C8 C7 C6 121.3(3) . . ?
C12 C7 C6 120.8(3) . . ?
C7 C8 C9 120.6(4) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 120.2(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 119.8(4) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.3(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 121.2(4) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
C18 C13 C14 118.2(4) . . ?
C18 C13 C6 121.9(3) . . ?
C14 C13 C6 119.9(3) . . ?
C15 C14 C13 121.0(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 120.4(4) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.8(4) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 120.1(4) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 120.6(4) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C6 -107.6(4) . . . . ?
C1 C2 C3 C4 68.9(4) . . . . ?
C6 C3 C4 C5 -134.7(4) . . . . ?
C2 C3 C4 C5 48.7(5) . . . . ?
C3 C4 C5 Br1 60.9(4) . . . . ?
C4 C3 C6 C7 -169.8(3) . . . . ?
C2 C3 C6 C7 6.5(5) . . . . ?
C4 C3 C6 C13 6.9(5) . . . . ?
C2 C3 C6 C13 -176.7(3) . . . . ?
C3 C6 C7 C8 52.5(5) . . . . ?
C13 C6 C7 C8 -124.4(4) . . . . ?
C3 C6 C7 C12 -132.1(4) . . . . ?
C13 C6 C7 C12 51.0(4) . . . . ?
C12 C7 C8 C9 -0.1(6) . . . . ?
C6 C7 C8 C9 175.4(4) . . . . ?
C7 C8 C9 C10 -0.1(7) . . . . ?
C8 C9 C10 C11 0.3(7) . . . . ?
C9 C10 C11 C12 -0.2(7) . . . . ?
C10 C11 C12 C7 -0.1(7) . . . . ?
C8 C7 C12 C11 0.2(6) . . . . ?
C6 C7 C12 C11 -175.3(4) . . . . ?
C3 C6 C13 C18 83.5(5) . . . . ?
C7 C6 C13 C18 -99.4(4) . . . . ?
C3 C6 C13 C14 -98.8(4) . . . . ?
C7 C6 C13 C14 78.3(4) . . . . ?
C18 C13 C14 C15 0.9(6) . . . . ?
C6 C13 C14 C15 -176.9(4) . . . . ?
C13 C14 C15 C16 0.2(7) . . . . ?
C14 C15 C16 C17 -0.7(7) . . . . ?
C15 C16 C17 C18 0.1(7) . . . . ?
C14 C13 C18 C17 -1.4(6) . . . . ?
C6 C13 C18 C17 176.3(4) . . . . ?
C16 C17 C18 C13 1.0(7) . . . . ?

_refine_diff_density_max         0.783
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.060



